Dear colleagues,
I would like to invite you to the lecture by Antonio Conte called "A Different Approach to the Passerini 3CR Tetrazole Using Ultrasound Irradiation". The lecture will be on Wednesday February 25th at 9AM in room 1.09 at IMTM.
Abstract
A Different Approach to the Passerini 3CR Tetrazole Using Ultrasound Irradiation
1,5-Disubstituted tetrazoles obtained via the Passerini three-component reaction are valuable scaffolds in medicinal chemistry, acting as bioisosteres of carboxylic acids and amides and enabling rapid access to diverse compound libraries. Developing faster, greener, and automated routes to these motifs is therefore highly relevant for drug discovery.
We report an ultrasound-assisted Passerini 3CR–tetrazole protocol optimized to eliminate chromatographic purification. Solvent screening identified 20% MeOH/H₂O as the optimal medium, promoting direct product precipitation and simple isolation by filtration. A broad chemical space was explored using automated, miniaturized synthesis to identify suitable substrate combinations. Selected reactions were then scaled up and performed using an OT-2 platform to reproducibly generate and collect the precipitated materials for full characterization.
This workflow integrates solvent engineering, ultrasound activation, and automation to provide a rapid and chromatography-free route to 1,5-disubstituted tetrazole libraries.